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Puerto Rico Cruises Starting In October 2026 and 2027

If you're looking at joining a cruise to Puerto Rico in October 2026 or 2027, we have 28 unique cruise itineraries and 133 departures available, operated by seven of the world's leading cruise lines departing in October.
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28 Cruises (133 Cruise Departures)
13 Day Halloween Transatlantic from Spain with Virgin Voyages
Cruise
 (1)

13 Days (12 Nights) Barcelona to San Juan
Cruise Line: Virgin Voyages
Ship: Scarlet Lady
Departure: 31 October 2027
Visit: Spain, Morocco, Puerto Rico
Inside
$1,259
Oceanview
$1,428
Balcony
$1,485
Suite
$4,610
From
US$1,259
Per Person
View Trip
16 Day MSC Grand Voyages with MSC Cruises
Cruise
 (1)

16 Days (15 Nights) Palma de Mallorca to Orlando
Cruise Line: MSC Cruises
Ship: MSC Grandiosa
Departure: 30 October 2026
Visit: Spain, Portugal, Puerto Rico, USA
Inside
$802
Oceanview
$1,014
Balcony
$1,189
Suite
-
From
US$802
Per Person
View Trip
15 Day MSC Grand Voyages with MSC Cruises
Cruise
 (1)

15 Days (14 Nights) Barcelona to Orlando
Cruise Line: MSC Cruises
Ship: MSC Grandiosa
Departure: 31 October 2026
Visit: Spain, Portugal, Puerto Rico, USA
Inside
$674
Oceanview
$834
Balcony
$1,053
Suite
$2,317
From
US$674
Per Person
View Trip
14 Day MSC Grand Voyages with MSC Cruises
Cruise
 (1)

14 Days (13 Nights) Barcelona to Miami
Cruise Line: MSC Cruises
Ship: MSC Grandiosa
Departure: 31 October 2026
Visit: Spain, Portugal, Puerto Rico, USA
Inside
$615
Oceanview
$761
Balcony
$936
Suite
-
From
US$615
Per Person
View Trip
8 Day Eastern Caribbean with St. Kitts with Princess
Cruise
 (6)

8 Days (7 Nights) Fort Lauderdale to Fort Lauderdale
Cruise Line: Princess
Ships: Island Princess, Sky Princess
Departures: Oct 2027 to Feb 2028
Visit: USA, Dominican Republic, Puerto Rico, Saint Kitts and Nevis
Princess Standard
Inside
$559
Oceanview
$664
Balcony
$714
Suite
$1,149
From
US$559
Per Person
View Trip
14 Day West Indies to Spain with Viking Cruises
Cruise
 (5)

14 Days (13 Nights) Barcelona to San Juan
Cruise Line: Viking Cruises
Ship: Viking Sea
Departure: 23 October 2026
Visit: Spain, Portugal, Sint Maarten, Puerto Rico
Viking $999 Air Deal
Exclusive Savings
Inside
-
Oceanview
-
Balcony
$3,299
Suite
$5,999
From
US$3,299
Save 200
Per Person
View Trip
9 Day Eastern Caribbean & Perfect Day with Royal Caribbean
Cruise

9 Days (8 Nights) Orlando to Orlando
Cruise Line: Royal Caribbean
Ship: Adventure of the Seas
Departures: Sep 2026 to Oct 2026
Visit: USA, Virgin Islands, Puerto Rico, Bahamas
Exclusive Savings
Inside
$647
Oceanview
$980
Balcony
$1,315
Suite
$2,437
From
US$647
Save 460
Per Person
View Trip
8 Day Eastern Caribbean & Perfect Day with Royal Caribbean
Cruise

8 Days (7 Nights) Miami to Miami
Cruise Line: Royal Caribbean
Ship: Allure of the Seas
Departure: 25 October 2026
Visit: USA, Bahamas, Puerto Rico, Dominican Republic
Exclusive Savings
Inside
$951
Oceanview
$1,251
Balcony
$1,143
Suite
$3,408
From
US$951
Save 532
Per Person
View Trip
8 Day Eastern Caribbean & Perfect Day with Royal Caribbean
Cruise

8 Days (7 Nights) Miami to Miami
Cruise Line: Royal Caribbean
Ship: Icon Of The Seas
Departures: Jun 2026 to Oct 2026
Visit: USA, Virgin Islands, Puerto Rico, Bahamas
Exclusive Savings
Inside
$1,227
Oceanview
$1,654
Balcony
$1,636
Suite
$2,629
From
US$1,227
Save 840
Per Person
View Trip
8 Day Eastern Caribbean with Puerto Rico with Princess
Cruise

8 Days (7 Nights) Orlando to Orlando
Cruise Line: Princess
Ship: Caribbean Princess
Departures: Jul 2026 to Oct 2026
Visit: USA, Puerto Rico, Dominican Republic, Turks and Caicos Islands
Princess Standard
Inside
$571
Oceanview
$621
Balcony
$956
Suite
$1,199
From
US$571
Per Person
View Trip
8 Day Caribbean And Antilles with MSC Cruises
Cruise

8 Days (7 Nights) Miami to Miami
Cruise Line: MSC Cruises
Ship: MSC World America
Departures: May 2026 to Mar 2028
Visit: USA, Dominican Republic, Puerto Rico, Bahamas
Inside
$567
Oceanview
$763
Balcony
$897
Suite
$1,444
From
US$567
Per Person
View Trip
10 Day Eastern Caribbean & Perfect Day with Royal Caribbean
Cruise

10 Days (9 Nights) New York to New York
Cruise Line: Royal Caribbean
Ship: Oasis of the Seas
Departure: 25 October 2026
Visit: USA, Bahamas, Puerto Rico, Dominican Republic
Exclusive Savings
Inside
$1,075
Oceanview
$1,461
Balcony
$1,321
Suite
$3,694
From
US$1,075
Save 630
Per Person
View Trip
8 Day Perfect Day Cococay & East Caribbean with Royal Caribbean
Cruise

8 Days (7 Nights) Orlando to Orlando
Cruise Line: Royal Caribbean
Ship: Star Of The Seas
Departures: May 2026 to Oct 2027
Visit: USA, Bahamas, Puerto Rico, Saint Martin
Bonus Onboard Credit
Exclusive Savings
Inside
$1,193
Oceanview
$1,544
Balcony
$1,609
Suite
$2,955
From
US$1,193
Save 933
Per Person
View Trip
20 Day MSC Grand Voyages with MSC Cruises
Cruise
 (1)

20 Days (19 Nights) Genoa to Orlando
Cruise Line: MSC Cruises
Ship: MSC Grandiosa
Departure: 26 October 2026
Visit: Italy, Spain, Portugal, Puerto Rico, USA
Inside
$983
Oceanview
$1,223
Balcony
$1,465
Suite
$3,308
From
US$983
Per Person
View Trip
19 Day MSC Grand Voyages with MSC Cruises
Cruise
 (1)

19 Days (18 Nights) Genoa to Miami
Cruise Line: MSC Cruises
Ship: MSC Grandiosa
Departure: 26 October 2026
Visit: Italy, Spain, Portugal, Puerto Rico, USA
Inside
$918
Oceanview
$1,145
Balcony
$1,307
Suite
$3,181
From
US$918
Per Person
View Trip
9 Day Eastern Caribbean with Puerto Rico with Princess
Cruise
 (1)

9 Days (8 Nights) Fort Lauderdale to Fort Lauderdale
Cruise Line: Princess
Ship: Regal Princess
Departures: Oct 2026 to Feb 2027
Visit: USA, Saint Martin, Puerto Rico, Dominican Republic, Turks and Caicos Islands
Princess Standard
Inside
$649
Oceanview
-
Balcony
$849
Suite
$1,029
From
US$649
Per Person
View Trip
8 Day Southern Caribbean Cruise with Royal Caribbean
Cruise
 (1)

8 Days (7 Nights) San Juan to San Juan
Cruise Line: Royal Caribbean
Ship: Rhapsody of the Seas
Departures: Sep 2026 to Oct 2026
Visit: Puerto Rico, Virgin Islands, Saint Martin, Antigua and Barbuda, Dominica
Exclusive Savings
Inside
$598
Oceanview
$750
Balcony
$1,149
Suite
$1,604
From
US$598
Save 555
Per Person
View Trip
16 Day Caribbean And Antilles with MSC Cruises
Cruise
 (1)

16 Days (15 Nights) Orlando to Orlando
Cruise Line: MSC Cruises
Ship: MSC Grandiosa
Departure: 30 October 2027
Visit: USA, Bahamas, Mexico, Dominican Republic, Puerto Rico
Inside
$1,359
Oceanview
$1,559
Balcony
$1,919
Suite
$3,489
From
US$1,359
Per Person
View Trip
10 Day Bermuda & Caribbean Cruise: New York, Bermuda & St. Marteen with Azamara Cruises
Cruise
 (3)

10 Days (9 Nights) New York to San Juan
Cruise Line: Azamara Cruises
Ships: Azamara Journey, Azamara Quest
Departures: Oct 2026 to Oct 2027
Visit: USA, Bermuda, Saint Martin, Virgin Islands, Puerto Rico
Azamara Always Included
Inside
$1,439
Oceanview
$1,999
Balcony
$2,489
Suite
$4,339
From
US$1,439
Per Person
View Trip
8 Day Southern Caribbean Cruise with Royal Caribbean
Cruise
 (1)

8 Days (7 Nights) San Juan to San Juan
Cruise Line: Royal Caribbean
Ships: Grandeur of the Seas, Rhapsody of the Seas
Departures: May 2027 to Apr 2028
Visit: Puerto Rico, Virgin Islands, Sint Maarten, Saint Lucia, Barbados
Bonus Onboard Credit
Exclusive Savings
Inside
$674
Oceanview
$749
Balcony
$1,215
Suite
$1,473
From
US$674
Save 571
Per Person
View Trip
18 Day MSC Grand Voyages with MSC Cruises
Cruise
 (1)

18 Days (17 Nights) Rome to Orlando
Cruise Line: MSC Cruises
Ship: MSC Grandiosa
Departure: 28 October 2026
Visit: Italy, Spain, Portugal, Puerto Rico, USA
Inside
$837
Oceanview
$1,047
Balcony
$1,266
Suite
$6,734
From
US$837
Per Person
View Trip
8 Day Southern Caribbean Halloween Cruise with Virgin Voyages
Cruise
 (2)

8 Days (7 Nights) San Juan to San Juan
Cruise Line: Virgin Voyages
Ship: Valiant Lady
Departure: 31 October 2026
Visit: Puerto Rico, Curacao, Aruba, Martinique, Saint Kitts and Nevis
Inside
$1,113
Oceanview
$1,323
Balcony
$1,533
Suite
$4,123
From
US$1,113
Per Person
View Trip
17 Day MSC Grand Voyages with MSC Cruises
Cruise
 (1)

17 Days (16 Nights) Rome to Miami
Cruise Line: MSC Cruises
Ship: MSC Grandiosa
Departure: 28 October 2026
Visit: Italy, Spain, Portugal, Puerto Rico, USA
Inside
$818
Oceanview
$1,009
Balcony
$1,248
Suite
$6,370
From
US$818
Per Person
View Trip
9 Day Perfect Day Cococay & East Caribbean with Royal Caribbean
Cruise

9 Days (8 Nights) Fort Lauderdale to Fort Lauderdale
Cruise Line: Royal Caribbean
Ships: Allure of the Seas, Symphony of the Seas
Departures: Jun 2026 to Oct 2027
Visit: USA, Saint Kitts and Nevis, Saint Martin, Puerto Rico, Bahamas
Bonus Onboard Credit
Exclusive Savings
Inside
$874
Oceanview
$989
Balcony
$1,056
Suite
$2,917
From
US$874
Save 750
Per Person
View Trip
9 Day Baltimore To San Juan Cruise with Royal Caribbean
Cruise

9 Days (8 Nights) Baltimore to San Juan
Cruise Line: Royal Caribbean
Ship: Vision of the Seas
Departure: 21 October 2027
Visit: USA, Turks and Caicos Islands, Aruba, Curacao, Puerto Rico
Bonus Onboard Credit
Exclusive Savings
Inside
$664
Oceanview
$804
Balcony
$1,636
Suite
$2,182
From
US$664
Save 383
Per Person
View Trip
8 Day Eastern Caribbean With Puerto Rico & Celebration Key with Princess
Cruise

8 Days (7 Nights) Orlando to Orlando
Cruise Line: Princess
Ship: Star Princess
Departures: Oct 2027 to Feb 2028
Visit: USA, Bahamas, Dominican Republic, Puerto Rico, Turks and Caicos Islands
Princess Standard
Sanctuary Collection
Inside
$699
Oceanview
$899
Balcony
$949
Suite
$1,299
From
US$699
Per Person
View Trip
15 Day Eastern/Western Caribbean Adventurer with Princess
Cruise

15 Days (14 Nights) Orlando to Orlando
Cruise Line: Princess
Ship: Caribbean Princess
Departures: Sep 2026 to Oct 2026
Visit: USA, Puerto Rico, Dominican Republic, Turks and Caicos Islands, Bahamas
Princess Standard
Inside
$1,088
Oceanview
$1,226
Balcony
-
Suite
-
From
US$1,088
Per Person
View Trip
10 Day Boston To San Juan Cruise with Celebrity Cruises
Cruise

10 Days (9 Nights) Boston to San Juan
Cruise Line: Celebrity Cruises
Ship: Celebrity Summit
Departure: 20 October 2027
Visit: USA, Dominican Republic, Virgin Islands, Antigua and Barbuda, Puerto Rico
Exclusive Savings
Inside
$1,004
Oceanview
$1,054
Balcony
$1,229
Suite
$4,129
From
US$1,004
Save 526
Per Person
View Trip
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